(3,3a,4,5,6,6a-hexahydropentalen-1-yloxy)trimethylsilane | 132865-38-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3,3a,4,5,6,6a-hexahydropentalen-1-yloxy)trimethylsilane
• 英文别名: [(3aR,6aR)-3,3a,4,5,6,6a-hexahydropentalen-1-yl]oxy-trimethylsilane
• CAS: 132865-38-4；137880-43-4
• 化学式: C₁₁H₂₀OSi
• 分子量: 196.365
• InChiKey: OHKUZPLTEJJCEU-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3,3a,4,5,6,6a-hexahydropentalen-1-yloxy)trimethylsilane 在 臭氧 、 2,3-二巯基丁二酸 作用下， 生成 (1S,2S)-2-(2-Oxo-ethyl)-cyclopentanecarboxylic acid
  参考文献：
  名称：

  Palladium-mediated transannular cyclizations of medium-ring olefinic enolsilanes

  摘要：

  Medium-ring olefinic ketone and lactone enolsilanes were subjected to palladium(II)-mediated cycloalkenylation conditions. Diverse bicyclic ring products were obtained in moderate to good yields. The effect of olefin geometry and ring size is discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.125
• 作为产物：
  描述：

  三甲基氯硅烷 、 cis-bicyclo[3.3.0]octan-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (3,3a,4,5,6,6a-hexahydropentalen-1-yloxy)trimethylsilane
  参考文献：
  名称：

  Palladium-mediated transannular cyclizations of medium-ring olefinic enolsilanes

  摘要：

  Medium-ring olefinic ketone and lactone enolsilanes were subjected to palladium(II)-mediated cycloalkenylation conditions. Diverse bicyclic ring products were obtained in moderate to good yields. The effect of olefin geometry and ring size is discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.125

文献信息

• Two Carbon Ring Expansion by Photochemical Ring Opening of Electrophilic Cyclobutenes
  作者：Michel Miesch、Gaëtan Mislin、Michel Franck-Neumann

  DOI：10.1016/s0040-4039(97)10032-6

  日期：1997.10

  The photolysis of electrophilic cyclobutenes condensed to a diquinanic moiety and bearing either an amino group or a hydroxyl group at the ring junction leads to the corresponding hydroazulenic derivatives in high yields. © 1997 Elsevier Science Ltd.

  亲电子化的环丁烯缩合成二喹啉部分并在环结处带有氨基或羟基的光解反应可高产率地得到相应的氢az嗪衍生物。©1997爱思唯尔科学有限公司。
• Photochemical, Thermal, and Base-Induced Access to Hydroazulene Derivatives via Two-Carbon Ring-Enlargement Reactions of Condensed Electrophilic Cyclobutenes
  作者：Gaëtan L. Mislin、Michel Miesch

  DOI：10.1021/jo025913l

  日期：2003.1.1

  Enamines, silyl enol ethers, and beta-keto ester anions derived from bicyclo[3.3.0]octan-2-one efficiently underwent a formal [2 + 2] cycloaddition reaction with DMAD and ethyl propynoate leading to a large variety of electrophilic cyclobutenes. The latter were transformed into polyfunctionalized bicyclo[5.3.0]decane (or hydroazulene) ring systems in high yields by fragmentation of the cyclobutene

  衍生自双环[3.3.0] octan-2-one的烯胺，甲硅烷基烯醇醚和β-酮酯阴离子与DMAD和丙酸乙酯进行了正式的[2 + 2]环加成反应，从而形成了多种亲电性环丁烯。通过环丁烯部分的断裂，后者以高收率转化成多官能化的双环[5.3.0]癸烷（或氢杂氮烯）环系统。这些两个碳原子的扩环反应被用作合成工具，用于构建代表丁二酚三环骨架的潜在前体的多官能化氢azulene衍生物。
• An efficient method for hydroazulenone from bicyclo[3.3.0]octanone via two carbon annulation
  作者：Chwang Siek Pak、Sung Kee Kim、Hyeon Kyu Lee

  DOI：10.1016/s0040-4039(00)79451-2

  日期：1991.10

  Hydroazulenones and hydroazulenediones are prepared efficiently from bicyclo[3.3.0]octanones via two carbon annulation utilizing thermal [2+2] cycloaddition of dichloroketene and fluoride or chloride induced fragmentation of the cycloadduct.

  由双环[3.3.0]辛烷酮通过二碳烯酮的热[2 + 2]环加成反应和氟化物或氯化物引起的环加成物的裂解，通过两次碳成环反应，可以高效地制备双环[3.3.0]辛酮和双氢酮。